CAS: 486-39-5; (S)-1-(4-Hydroxybenzyl)-6-Methoxy-1,2,3,4-Tetrahydroisoquinolin-7-Ol

该化合物是帕帕韦罗塞亚家族的植物品种,它是碱性藻类,无色的黄色晶体化合物,显示一系列生物活动,包括潜在的抗炎和止痛性能;Coclaurine在结构上与其他alkales相似,允许它与其他生物目标,包括...

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CAS号3423-07-2 1α-(4-Hydroxybe...

合成工艺路线路线简述

    对羟基苯乙胺置于sodium Pyruvate,Candidatus Nitrosopumilus Salaria Cell Lysate Containing Bd31 Tyrosinase,Chromobacterium Violaceum Cell Lysate Containing Transaminase,Myxococcus Xanthus Cell Lysate Containing Catechol-O-Methyltransferase,Wild-Type Thalictrum Flavum Cell Lysate Containing Norcoclaurinesynthase,Sodium Hydroxide,Magnesium Chloride体系中,用 Aq. Buffer 作为反应溶剂,化学反应 9.5H,反应生成 衡州乌药碱; 乌药碱
    参考文献:结合甲基转移酶的多酶一锅级联用于四氢异喹啉生物碱的战略多样化
    标题:结合甲基转移酶的多酶一锅级联用于四氢异喹啉生物碱的战略多样化
    摘要:四氢异喹啉 (Thiq) 环系统存在于多种结构多样的天然产物中,表现出广泛的生物活性.通过在体外建立级联反应来模拟此类生物碱的生物合成途径,是一种成功的策略,并且可以提供比传统合成方法更好的立体选择性. S-腺苷甲硫氨酸 (Sam) 依赖性甲基转移酶对于 Thiq 的生物合成和多样化至关重要;然而,由于 Sam 成本高和底物范围小,它们的体外应用往往受到限制.在这项研究中,我们描述了甲基转移酶在体外多酶级联中的应用,包括原位反应生成 Sam.在酶制备规模上,使用多达七种酶对天然和非天然 Thiq 进行区域选择性多样化.甲基转移酶的区域选择性取决于 C-1 处的基团和 Thiq 中氟的存在.所使用的儿茶酚甲基转移酶还发现了有趣的双重活性,该酶能够区域选择性地甲基化单个分子中的两种不同的儿茶酚.
    DOI:10.1002/anie.202104476

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    专利信息


    专利号:US-12091696-B2
    优先权日:2022-08-10
    标 题 :O-methyltransferase protein with highly specific catalytic function for multiple bias parent nuclei and encoding gene and use thereof
    发明人:CHEN SHA; YU YUETONG
    权利人:INST CHINESE MATERIA MEDICA CHINA ACADEMY OF CMS
    摘要:The present disclosure provides an O-methyltransferase protein with a highly specific catalytic function for multiple benzylisoquinoline alkaloids (BIAs) parent nuclei and an encoding gene and use thereof. Compared with wild-type O-methyltransferase, the O-methyltransferase protein (SEQ ID NO: 2) shows an enhanced enzymatic activity and a wider substrate scope. The O-methyltransferase protein can catalyze O-methylation of backbones from three BIAs, including monobenzylisoquinolines (norcoclaurine, coclaurine, and N-methylcoclaurine), aporphines (asimilobine and N-methylasimilobine), and protoberberines (scoulerine and tetrahydrocolumbamine). Meanwhile, this O-methyltransferase protein is highly regioselective for each backbone. The O-methyltransferase protein catalyzes methylation of the monobenzylisoquinolines at 6-OH and 7-OH, is only active on 6-OH of the backbone of the aporphines, and mainly catalyzes methylation of the protoberberines at 2-OH. Moreover, the O-methyltransferase protein has a stronger catalytic activity and can be used as a biocatalyst for the semi-synthesis of related compounds.

    专利号:CN-106085981-A
    优先权日:2016-06-30
    标题 :Methyltransferase gene involved in the synthesis of sanguinarine and chelerythrine in Boluohui and its application

    专利号:CN-106119265-A
    优先权日:2016-06-30
    标题 :Cytochrome P450 enzyme gene involved in the synthesis of sanguinarine and chelerythrine in Boluohui and its application

    专利号:CN-106047904-A
    优先权日:2016-06-30
    标 题 :The flavoprotein oxidase gene involved in the synthesis of sanguinarine and chelerythrine in Boluohui and its application

    专利号:CN-114891840-A
    优先权日:2022-05-23
    标 题 :Application of lotus leaf O-methyltransferase and its encoding gene in the synthesis of benzylisoquinoline alkaloids and phenylpropionic acids

    专利号:CN-114891840-B
    优先权日:2022-05-23
    标题:Lotus leaf O-methyltransferase and application of encoding gene thereof in synthesis of benzyl isoquinoline alkaloid and phenylpropionic acid compounds
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    主要参考文献


    1: Bennett MR, Thompson ML, Shepherd SA, Dunstan MS, Herbert AJ, Smith DRM, Cronin VA, Menon BRK, Levy C, Micklefield J. Structure and Biocatalytic Scope of Coclaurine N-Methyltransferase. Angew Chem Int Ed Engl. 2018 Aug 13;57(33):10600-10604. doi: 10.1002/anie.201805060. Epub 2018 Jun 28.
    2: Ali R, Jiao Y, Kerr Wall P, Patching SG, Ahmad I, Lutfulla G, dePamphilis CW. In silico identification and structure function analysis of a putative coclaurine N-methyltransferase from Aristolochia fimbriata. Comput Biol Chem. 2020 Apr;85:107201. doi: 10.1016/j.compbiolchem.2020.107201. Epub 2020 Jan 11. 9(11-12):1788-1793. doi: 10.1002/dta.2258. Epub 2017 Sep 15. 68(4):939-41. doi: 10.1271/bbb.68.939. 56(7):649-55. doi: 10.1016/s0031-9422(00)00481-7. 277(1):830-5. doi: 10.1074/jbc.M106405200. Epub 2001 Oct 26. 42(3):213-22. doi: 10.1055/s-2007-971630. 6(10):793-6. doi: 10.1248/bpb1978.6.793. 35(1):90-1. 45(3):136. doi: 10.1055/s-2007-971276. 17(9):641-6. Chinese.
    12:752211. doi: 10.3389/fphar.2021.752211.

    合成参考文献


    参考文献:10.1080/07391102.2012.741052
    摘要:Hung I, Chang S, Chang P, Lee C, Chen CY. Memory enhancement by traditional Chinese medicine Journal of Biomolecular Structure and Dynamics. 2013 Dec;31(12):1411–39. doi: 10.1080/07391102.2012.741052.
    参考文献:10.1002/rcm.8507
    摘要:Lommen A, Elaradi A, Vonaparti A, Blokland M, Nielen MW, Saad KA, Abushreeda WM, Horvatovich P, Al-Muraikhi AE, Al-Maadheed M, Georgakopoulos C. Ultra-fast retroactive processing of liquid chromatography high-resolution full-scan Orbitrap mass spectrometry data in anti-doping screening of human urine. Rapid Commun Mass Spectrom. 2019 Oct 30;33(20):1578–88. doi: 10.1002/rcm.8507.
    参考文献:10.1248/yakushi1947.86.4_296
    摘要:Lu ST. [Studies on the alkaloids of Formosan lauraceous plants. IX. Alkaloids of Cryptocarya chinensis Hemsl. and Cryptocarya konishii Hayata]. Yakugaku Zasshi. 1966 Apr;86(4):296–9. doi: 10.1248/yakushi1947.86.4_296.
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